Is what the questioner does—authorizing someone to perform Umrah on behalf of the deceased, mediating between him and relatives and friends, and paying the transfer fees from his own money without informing them—disliked or beloved, and will he be rewarded for it?

There is no harm in performing 'Umrah on behalf of the deceased or a living person who is incapacitated due to old age or an incurable illness. The one who does so will be rewarded. It is permissible to pay money to someone to perform 'Umrah, provided that a person characterized by goodness, righteousness, and knowledge of the rulings is chosen, and that he performs the act himself or informs his client that he will delegate someone else, because the client might not be pleased with someone else. It is not permissible for someone who has been appointed by more than one person for Hajj or 'Umrah to delegate someone else to perform it without the client's knowledge, as this falls under consuming wealth unjustly. Every assistance in such a righteous deed will be rewarded.